No Regrets, Just Love
by Scarlett Rogue
Summary: When Dean tries to give Cas a sensual massage the boys get a bit carried away. Cas is ready to lose his virginity, and Dean just wants to make sure he'll never regret it.


Taken from my AO3 account, Scarlett_Rogue. Enjoy, and please review!

Warnings: Fingering, Massage, First Time, Dirty Talk.

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"_Dean_," Cas whispered, arching his back in to Dean's touch. The hunter's nimble fingers dug into hard muscles, loosening them up, relieving Cas of the tension he had been storing for months now ever since he got out of Purgatory.

"You know how awkward it's gonna be if Sam hears you?" Cas felt oily liquid squirted onto his back, felt Dean lap it up with his palms flat, fingers splayed out to massage every inch of the angel that he could get to.

"It isn't my fault that you are so g-_ah_, good at this."

Dean's chuckle shook the bed. His hands traveled lower down the Angel's back, rubbing against his dimples before pushing the sheet down further. Cas sighed, not even thinking about what this action meant. He was an angel, after all - and not a very sexually active one, either. His biggest sexual encounter thus far had been in the back of the Impala, Dean laying on his back, Cas above him, rutting their erections together until they both came in their pants. It was wonderful, but fast, and no where near as intimate as this.

This was Heaven.

Cas' legs spread without his permission, only a few inches, but enough to draw Dean's attention. He took the hint and cupped Cas' firm ass in both hands, squeezing gently, smearing massage oil over his rounded cheeks.

More oil was squirted over his backside, collected quickly by Dean's skilled fingers, and Cas bent his knee and raised one leg as Dean's fingers drifted down the crack of his ass, lightly skimming over his hole. He moaned softly and pressed back against those fingers. Dean was toying with him, stroking his thighs, the backs of his knees, bringing his hand back up to spread his cheeks, one finger grazing his puckered hole.

"_Dean_, more," Cas gasped. One oily finger circling his hole, his hips bucking back as Dean pressed the tip in, feeling Cas flutter around his finger.

"I don't want to hurt you," Dean said. He had removed his finger and was letting it circle Cas' hole once more, his other hand rubbing down Castiel's spine.

"I'm an angel," Cas said. "And you're human. I can assure you, it will not hurt me."

Dean arched an eyebrow, remembered back to the time he had punched Cas in the face and felt like he had broken his own hand, and nodded. Made sense. He pushed one finger in all the way to the knuckle, closing his eyes tight at the soft keening noise Cas emitted. He crooked his finger, earning him the closest thing to a whine he had ever heard from his angel as his index finger pushed against Cas' prostate. Castiel's hips jerked forward, cock rutting against the mattress. Dean pushed another finger in next to the first, surprised by how tight but easy it was to get them both in. Cas had been right, of course; Dean couldn't really hurt him.

He set a slow pace, working his fingers in and out of Cas' tight ass, watching smugly as Cas seemed to struggle with his desire to both hump the mattress and fuck himself on Dean's fingers. He seemed to come to a conclusion, and Dean had to hold Cas' hips still when he started pushing his ass back hard against Dean's hand. It wasn't going to be like that, not this time, at least. This time was going to be slow and gentle, the way Cas' first time ought to be.

The way _his_ first time ought to have been, Dean thought grimly. But being with Cas was like starting over. Even Dean, with all his experience, was flying blind most of the time. As terrifying as it was, it was also incredibly liberating. He got to do everything over again, the right way, and share it all with someone he loved.

Someone who, by this point, was squirming underneath Dean, moaning out foreign words, random, beautiful trills with his name mingled in, and even _that_ sounded beautiful mixed in with Cas' whispered groans. It was like music; music that made Dean want to press Cas into the mattress and fuck him until he couldn't see straight, but music all the same.

"It's okay, Cas, I got you. Just calm down, feel it."

"Feel it?" His hips snapped back harshly into Dean's hand and they groaned in unison. Dean pressed another finger in, fucking all three slowly into the angel, eyes glistening with lust and awe as they disappeared in the wet heat. "I _am_ feeling it, Dean. I want to feel _more_!"

Alright, so maybe introducing Cas to something like this after such a stressful day wasn't the best timing in the world, but Dean couldn't for the life of him bring himself to regret it. He pulled his fingers out, head spinning as Cas whined and cursed under his breath, and pressed his body down on top of Cas. He ran his lips over the shell of Cas' right ear and smirked as Cas shivered under him.

"What do you want, baby?"

"_You_."

"Mm, not good enough. What do you _want_?"

"Dean," Cas moaned, burying his face in the pillow. Dean ran his fingers through the dark hair and peppered his neck with kisses.

"Just tell me what you want, Cas. I'll do whatever you want, but only if you're absolutely positive that you're ready, that you won't regret anything." His cock was straining against the denim pants, and he was suddenly regretting not wearing underwear. The friction was becoming painful. He knew what he wanted, but he couldn't, wouldn't take it, not if he thought for a second that Cas would regret it. Maybe he couldn't exactly rewind time and redo all the things in his early life that had been rushed or screwed up, but it wasn't too late for Cas.

"I want-" Cas gasped as Dean sucked his neck softly. "I want you inside me. I want you to be my first."

"Are you sure?" Dean asked. Before he knew it Cas had rolled out from under him, dragged Dean on top of him so they were face to face.

"Yes, Dean, I'm sure. I wouldn't ask this of anyone else." His lips twitched in that familiar way that Dean had come to know as not just any smile, but _his_ smile. He kissed Cas then, sweeping his tongue over those chapped lips, and sighed as Cas' hands traveled to his pants and unbuttoned them, freeing his aching cock from it's confines. He groaned into Cas' mouth and the angel pushed Dean into a sitting position, pulled himself up and sat in his lap. Dean raised an eyebrow at him.

"Cowboy?" He grinned, amused.

"Shut up," Cas blushed.

Dean groaned as Cas grasped his cock in hand and pressed his wet hole against the tip. He immediately felt the oil from Cas' stretched hole drip onto his cock and thanked Heaven he had thought to get the massage oil/lube combo. It was a bitch to find, an even bigger bitch to put up with Sam's jokes when he saw it, but worth it in the end.

"Holy fuck," Dean gasped as Cas sank all the way down on his cock, body pressed down flat against his legs. Cas was biting his bottom lip and his eyes were glazed over. He looked so different, desire pooling in his sapphire eyes, and Dean rocked up into his body to test the waters. The result was unforgettable: Cas' eyes widening, head falling back as a deep groan ripped from his throat, gravel sending shock waves down Dean's spine. Cas gripped Dean's shoulders and looked him dead in the eye.

"Fuck me, Dean." It was less of an invitation and more of a demand, and that thought had Dean gripping his hips tight and thrusting upward, small noises pulling from his throat that would have embarrassed him at any other moment, but Cas was lifting himself up and dropping himself on Dean's cock, riding him like it was the hundredth time rather than the first, demanding to be taken, and _fuck_, if that wasn't the hottest thing Dean had ever seen.

"Oh God, oh Dean, faster, please Dean..."

Dean wrapped his arms around Cas' waist, took a second to marvel to how small he was without the trench coat, then dragged them both backward. His back hit the mattress, Cas' chest pressed down on his, and he used the new position to snap his hips up, cock sliding in and out of Cas' ass, oil spilling out around the edges, the faintest hint of cloudy coloring as it mixed with Dean's pre-come.

"Cas, you're so fucking perfect, _fuck_, I could do this all day..."

"Liar," Cas grinned into his neck. It earned him a harsh snap of Dean's hips, and Cas cried out as the head of Dean's cock hit his prostate full force. He pushed himself up, wiggled his hips a little, and started riding Dean, mouth dropping open in shock and pleasure as each thrust hammered hard against that spot, sending him closer and closer to the edge. Dean felt the muscles in Cas' ass flutter around his cock, tighten and relax, and he knew it was voluntary. Cas was getting close fast and wanted to bring Dean off with him, and damn was he doing a good job of it!

"Fuck, Cas, I'm gonna come, _shit_ I'm gonna come in your ass-"

Cas slammed down once more, at the same time capturing Dean's lips against his own, and Dean filed the next few seconds in his memory forever. Cas trembled above him, legs shaking violently, and he moaned into Dean's mouth as he came hard, cock twitching and spurting out against Dean's abdomen. The thought that he made an angel of the lord come sent him over the edge, and he drained himself in Cas' ass, egged on by those muscles clenching around his member. He gasped, pulled away from Cas' lips to suck in breath after deep breath, his arms wrapping around Cas to support him as he too reminded himself how to breathe.

"Cas," Dean breathed out. The angel rolled off him but kept one leg slung over his waist. He brushed his lips over Dean's shoulder and smiled.

"Dean," he said, half exhausted and half giddy on post orgasm endorphins.

It took some minutes for them to say much more, but after a while Dean grasped Cas' thigh and rolled them on their sides, slotting his leg between the angel's and holding him far enough to look into his eyes.

"So, was that...I dunno, good for you?"

Cas let out an odd, uncharacteristic giggle, a short burst of air that stopped almost as fast as it started. "It was...spectacular. Perfect."

"Really?"

"You were wonderful, Dean."

"Now you're just stroking my ego." Cas let out another odd little giggle (what Dean would later come to call 'the sex giggle') and pressed their lips together.

"It was everything I had never wanted, never even thought about, until you walked into my life. It, and you, are _everything_."

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Please review, otherwise I tend to remove these if they have zero reviews after a certain amount of time (or favorites). I take requests, so if you've got something in mind I can always use the inspiration. My tumblr is someottersmarryhedgehogs, LJ is team_free_smut, and AO3 is Scarlett_Rogue, so yeah, I get around. Don't hesitate if you have a prompt or questions!


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